US3973945A - Pyran-2,4-dione derivatives - Google Patents

Pyran-2,4-dione derivatives Download PDF

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Publication number
US3973945A
US3973945A US05/526,746 US52674674A US3973945A US 3973945 A US3973945 A US 3973945A US 52674674 A US52674674 A US 52674674A US 3973945 A US3973945 A US 3973945A
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compound
carbon atoms
water
compounds
alkyl
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US05/526,746
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English (en)
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Akiharu Fujino
Isao Iwataki
Yoshihiko Hirono
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms

Definitions

  • the present invention relates to novel compounds of 3,4-dihydro-2H-pyrane-2,4-diones, the process for the preparation thereof and their uses as herbicides having selective activity.
  • this invention relates to herbicidal compositions containing one or more of novel compounds, and to the method of controlling weeds which comprises applying to plant or to soil the said compounds.
  • Another object is to provide an improved compositions and processes for killing undesired plants.
  • the inventors synthesized quite a few compound of 3,4-dihydro-2H-pyrane-2,4-dione derivatives and tested the biological activities the compounds.
  • novel compounds of this invention are characterized by the following formula: ##SPC2##
  • R 1 and R 2 are alkyl having six or less carbon atoms
  • R 3 is selected from the group consisting of alkyl having six or less carbon atoms and alkenyl having six or less carbon atoms, with the proviso that R 1 and R 2 don't both represent a methyl group
  • R 1 and R 2 are alkyl of 2 to 3 carbon atoms and R 3 is alkyl of 2 to 3 carbon atoms an allyl group. Particularly preferred because of its high order of herbicidal activity is: 3-(1-ethoxyamino-1-hydroxypropyl)-6-ethyl-3,4-dihydro-2H-pyrane-2,4-dione. But, those compounds were R 1 and R 2 both represent methyl don't have a superior herbicidal activity.
  • the compounds of this invention can be prepared in accordance with the following equation: ##SPC4##
  • R 1 , R 2 and R 3 are as previously defined.
  • the compounds of this invention are prepared through the reaction of general formula [IV] with water under the irradiation with light.
  • the above reaction can be conducted both in an inert solvent and in the absence of a solvent, but preferably in an inert solvent.
  • an inert solvent By using an inert solvent the compounds of this invention are obtained in high yield.
  • an inert solvent As an inert solvent, alcohol, acetone, ether, dioxane, chloroform, benzene and toluene, preferably acetone, are used. It is, in many cases, preferably to use the above solvent containing water of 1 to 10%, more preferably of 2 to 5%, as the reactant.
  • temperatures from the range of 0°-100°C, and preferably 10° - 35°C, are satisfactorily employed for the above reaction and the reaction terminates between 0.5 and 60 hours, in several days in some case.
  • ultraviolet light is preferably used and high-pressure mercury arc is ordinarily used as ultraviolet source.
  • the crude product is isolated from the reaction mixture by filtration or by extraction with a solvent.
  • a chemical structure of the resulting purified compound can be positively identified by means of elementary analysis, NMR spectrum and IR spectrum.
  • the starting compound [IV] can be prepared in accordance with the following equation: ##SPC6##
  • the compound of this invention may be formed as the intermediate in the process of above condensation reaction which implies the addition of formula [IX] and the fast elimination of a molecule of water.
  • the compounds of the invention are particularly effective in the control of grass weeds such as annual bluegrass (Poa annua L.); water foxtail (Alopecurus aequalis Sobol), large crabgrass (Digitaria adscendens Henr.), green foxtail (Seturia viridis Beauv), wild oat (Avena fatua L) etc. and they hardly injure broad leaf crops such as adzuki bean (Phaseolus angularis W. F. Wight) and soy bean (Glycine max Merrill) and sugar beets (Beta vulgaris L.) which easily suffer phyto-toxicity.
  • the compounds of the invention are the selective herbicide.
  • a chemical amount containing 250g of effective component as a matter of course, further a chemical amount containing 125g or less of effective ingredient, in proportion to 10 are of area, in compliance with the same treating method of conventional herbicide exhibits a strong herbicidal effect and thereby prevention and extermination of weeds can be expected.
  • the compounds of this invention can be applied directly to the soil as a pre-emergence treatment or to plant foliage as a post-emergence treatment, or they can be mixed intimately with the soil, preferably pre-emergence treatment to the soil, and may be applied to soil or plant foliar at rates of 50-1000g per 10 are, preferably about 100g per 10 are.
  • the method of the present invention comprehends the employment of a liquid or solid composition containing one or more of the present compounds as an active ingredient.
  • the active ingredient of this invention may be formulated by mixing with suitable carriers in a form generally used in agricultural chemicals such as wettable powder, emulsifiable concentrate, dust formulation, granular formulation, water soluble powder and aerosol.
  • suitable carriers such as wettable powder, emulsifiable concentrate, dust formulation, granular formulation, water soluble powder and aerosol.
  • solid carriers bentonite, diatomaceous earth, apatite, gypsum, talc, pyrophyllite, vermiculite, clay and others are used.
  • liquid carriers kerosene, mineral oil, petroleum, solvent naphtha, benzene, xylene, cyclohexane, cyclohexanone, dimethylformamide, alcohol, acetone, and others are used.
  • surface active agent are added in order to give a homogeneous and stable formulation.
  • the compounds of this invention also can be applied admixed with other chemicals which are used in agronomic and horticultural management and are compatible with the compounds of this invention.
  • Such chemicals can be, but are not restricted to, the classes of chemicals commonly known as plant nutrients, fertilizers, insecticides, acaricides, fungicides, herbicides and nematocides.
  • the compounds of the present invention be applied admixed with urea derivatives such as 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-urea, or N-(3,4-dichlorophenyl)N', N'-dimethylurea, triazine derivatives such as 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, or 2-chloro-4,6-bis(ethylamino)-s-triazine and amide derivatives such as N-1-naphthyl-phthalamic acid.
  • urea derivatives such as 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-urea, or N-(3,4-dichlorophenyl)N', N'-dimethylurea
  • triazine derivatives such as 2-chloro-4-ethylamino-6-isopropylamino-s-tria
  • concentrations of the active ingredients in the herbicidal composition of this invention vary according to type of formulation, and they are, for example, used in a range of 5 - 80 weight percent, preferably 10 - 60 weight percent, in wettable powder, 5 - 70 weight percent, preferably 20 - 60 weight percent, in emulsifiable concentrates, and 0.5 - 30 weight percent, preferably 1 - 10 weight percent in dust formulation.
  • a wettable powder or an emulsifiable concentrate produced thereto is diluted with water to a specified concentration and thereby, it is used as a liquid suspension or a liquid emulsion for treating soils or plant foliars. Further, a dust formulation is directly used for the soil treatment or the foliar treatment.
  • the non-limiting examples for the herbicidal composition are illustrated as follows:
  • an emulsifiable concentrate containing 40% of the active ingredient is obtained. In practical use, it is diluted to certain concentration with water and then is sprayed as an emulsion.
  • Fine particles are made into granules having the diameter in the range of 0.5 -- 1.0mm by granulator.
  • aqueous emulsion prepared by diluting an emulsifiable concentrate with water to a specified concentration was sprayed on the pot.
  • the pots were kept in a green house and water was added to the pot daily in order to keep the water level. Two weeks after spraying, the degrees of damage to the test plant was observed and estimated by the values of 0 - 5 which have the same meanings as those of Test 1.
  • FIG. 1 is the infrared spectrum of 3-(1-ethoxyamino-1-hydroxypropyl)-6-ethyl-3,4-dihydro-2H-pyrane-2,4-dione

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyrane Compounds (AREA)
US05/526,746 1973-12-05 1974-11-25 Pyran-2,4-dione derivatives Expired - Lifetime US3973945A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JA48-135274 1973-12-05
JP48135274A JPS5084571A (enrdf_load_stackoverflow) 1973-12-05 1973-12-05

Publications (1)

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US3973945A true US3973945A (en) 1976-08-10

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US05/526,746 Expired - Lifetime US3973945A (en) 1973-12-05 1974-11-25 Pyran-2,4-dione derivatives

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US (1) US3973945A (enrdf_load_stackoverflow)
JP (1) JPS5084571A (enrdf_load_stackoverflow)
BE (1) BE822920A (enrdf_load_stackoverflow)
BR (1) BR7410153A (enrdf_load_stackoverflow)
DE (1) DE2457599B2 (enrdf_load_stackoverflow)
FR (1) FR2253749A1 (enrdf_load_stackoverflow)
GB (1) GB1438420A (enrdf_load_stackoverflow)
NL (1) NL7415886A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4214963A (en) * 1977-12-06 1980-07-29 Javier Garcia de Lama Process for the preparation of substituted 4H-pyran-4-ones
US4544399A (en) * 1983-07-01 1985-10-01 Stauffer Chemical Company Certain 1,3-cyclohexanedione adducts of substituted phenoxyphenoxypropionic acids and their use as an herbicide
WO1988010258A1 (en) * 1987-06-17 1988-12-29 La Trobe University Human leucocyte elastase inhibitor compounds
US5981496A (en) * 1997-09-19 1999-11-09 Millennium Pharmaceutical, Inc. α-pyrones for treating α-pyrone responsive states

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7305083A (enrdf_load_stackoverflow) * 1972-04-11 1973-10-15

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7305083A (enrdf_load_stackoverflow) * 1972-04-11 1973-10-15

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4214963A (en) * 1977-12-06 1980-07-29 Javier Garcia de Lama Process for the preparation of substituted 4H-pyran-4-ones
US4544399A (en) * 1983-07-01 1985-10-01 Stauffer Chemical Company Certain 1,3-cyclohexanedione adducts of substituted phenoxyphenoxypropionic acids and their use as an herbicide
WO1988010258A1 (en) * 1987-06-17 1988-12-29 La Trobe University Human leucocyte elastase inhibitor compounds
US5981496A (en) * 1997-09-19 1999-11-09 Millennium Pharmaceutical, Inc. α-pyrones for treating α-pyrone responsive states

Also Published As

Publication number Publication date
DE2457599B2 (de) 1976-09-02
NL7415886A (nl) 1975-06-09
BE822920A (fr) 1975-04-01
GB1438420A (en) 1976-06-09
DE2457599A1 (de) 1975-06-12
BR7410153A (pt) 1976-06-08
JPS5084571A (enrdf_load_stackoverflow) 1975-07-08
FR2253749A1 (enrdf_load_stackoverflow) 1975-07-04

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